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Contents Vol 68(12)

Rhodium(ii) Azavinyl Carbenes and their Recent Application to Organic Synthesis

Samantha C. Hockey A B and Luke C. Henderson A B C
+ Author Affiliations
- Author Affiliations

A Strategic Research Centre for Chemistry and Biotechnology, Deakin University, Pigdons Road, Geelong, Vic. 3216, Australia.

B Institute for Frontier Materials, Deakin University, Pigdons Road, Geelong, Vic. 3216, Australia.

C Corresponding author. Email: luke.henderson@deakin.edu.au

Australian Journal of Chemistry 68(12) 1796-1800 https://doi.org/10.1071/CH15363
Submitted: 19 June 2015  Accepted: 5 October 2015   Published: 21 October 2015

Abstract

This highlight solely focusses on the synthetic applications of azavinyl rhodium(II) carbenes derived from N-sulfonyl triazoles. An overview of their use in intermolecular reactions to form a variety of heterocycles is examined, in addition to intramolecular annulations and rearrangements.


References

[1]  P. S. Skell, R. C. Woodworth, J. Am. Chem. Soc. 1956, 78, 4496.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG28XovV2jtg%3D%3D&md5=df6759c575079737908c5b730f7ea45cCAS |

[2]  D. Qian, J. Zhang, Chem. Soc. Rev. 2015, 44, 677.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFegs7zL&md5=ba090291e8b7aa3a7095eac5e5dfea30CAS | 25522173PubMed |

[3]  D. J. Cardin, B. Cetinkaya, M. J. Doyle, M. F. Lappert, Chem. Soc. Rev. 1973, 2, 99.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXksFegu7k%3D&md5=7f49e72f32fca84a62a8ae55df3a039aCAS |

[4]  E. O. Fischer, A. Maasbol, Angew. Chem. Int. Ed. Engl. 1964, 3, 580.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  H. M. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXksVChsr4%3D&md5=4de956348246038cbcf8fcf8c20f4317CAS | 12914484PubMed |

[6]  D. M. Hodgson, F. Y. T. M. Pierard, P. A. Stupple, Chem. Soc. Rev. 2001, 30, 50.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXkt1Ojuw%3D%3D&md5=cca193e35cd2e35abf8b11d2a2c3352aCAS |

[7]  D. S. Pedersen, A. Abell, Eur. J. Org. Chem. 2011, 2399.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvVWhu7c%3D&md5=cf646101ef99b2bdb269ad06e3863170CAS |

[8]  G. Aromí, L. A. Barrios, O. Roubeau, P. Gamez, Coord. Chem. Rev. 2011, 255, 485.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 2011, 6, 2696.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFSjur7P&md5=69f1bb4a9cba264bfb75c2a7d5764a68CAS | 21954075PubMed |

[10]  V. Hugenberg, B. Riemann, S. Hermann, O. Schober, M. Schafers, K. Szardenings, A. Lebedev, U. Gangadharmath, H. Kolb, J. Walsh, W. Zhang, K. Kopka, S. Wagner, J. Med. Chem. 2013, 56, 6858.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtF2rtbnP&md5=d8213f4a259b09ccb773da18b292e2b1CAS | 23899323PubMed |

[11]  H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpvVWkuro%3D&md5=88d5649f0124732f1dfb15478b0eb17fCAS | 14678739PubMed |

[12]  O. Dimroth, Justus Liebigs Ann. Chem. 1909, 364, 183.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaD1MXmt1Kh&md5=ea6f16d6606be1cde41587ce8d15f760CAS |

[13]  T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Cgsb3E&md5=2c0c03326c57eb14c4f8b0846879417aCAS | 18855475PubMed |

[14]  M. Zibinsky, V. V. Fokin, Angew. Chem. Int. Ed. 2013, 52, 1507.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVKgur7I&md5=9e45b5b4f00ecbf807e4165e70afbe9fCAS |

[15]  S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjslGns7o%3D&md5=9cefbc554b5f0022722d5633acd0698dCAS | 23477345PubMed |

[16]  T. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1470.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjtVSiurk%3D&md5=5c443351c31e7e7d94aaffcab7f704c8CAS |

[17]  T. Miura, K. Hiraga, T. Biyajima, T. Nakamuro, M. Murakami, Org. Lett. 2013, 15, 3298.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXpslCit70%3D&md5=b2d1beb4605493b945b9e8d3ad2521d6CAS | 23777199PubMed |

[18]  T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFGmtL3O&md5=2cdd0dd9176d59322e5319520d10b3b4CAS | 22129424PubMed |

[19]  S. Chuprakov, B. T. Worrell, N. Selander, R. K. Sit, V. V. Fokin, J. Am. Chem. Soc. 2014, 136, 195.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvFWltL7E&md5=fa7c8e41462f4cc0466f6c324f9256f2CAS | 24295389PubMed |

[20]  H. J. Jeon, D. J. Jung, J. H. Kim, Y. Kim, J. Bouffard, S. G. Lee, J. Org. Chem. 2014, 79, 9865.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhs1eju77O&md5=b9c2e5a4e37b4b4b05278d41821a7390CAS | 25259803PubMed |

[21]  J. He, Z. Man, Y. Shi, C. Y. Li, J. Org. Chem. 2015, 80, 4816.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmtF2gtbc%3D&md5=ac1e187a39b232309c191b268b3b3261CAS | 25855588PubMed |

[22]  Y. Z. Zhao, H. B. Yang, X. Y. Tang, M. Shi, Chem. – Eur. J. 2015, 21, 3562.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXosFOjtA%3D%3D&md5=88acf528353527d6af0f920dc3c3f147CAS | 25639462PubMed |

[23]  D. J. Jung, H. J. Jeon, J. H. Kim, Y. Kim, S. G. Lee, Org. Lett. 2014, 16, 2208.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXlsl2kt70%3D&md5=a22f8d11e8b586d31c7eca8430521e3dCAS |

[24]  C. E. Kim, S. Park, D. Eom, B. Seo, P. H. Lee, Org. Lett. 2014, 16, 1900.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXkslals7c%3D&md5=b3d0896f81d55d4837caab2a84745669CAS | 24660875PubMed |

[25]  F. Medina, C. Besnard, J. Lacour, Org. Lett. 2014, 16, 3232.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXptVaht70%3D&md5=73e1f74f5a7deaf88d9528a9eca9b9c0CAS | 24885761PubMed |

[26]  D. Yadagiri, P. Anbarasan, Chem. – Eur. J. 2013, 19, 15115.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1Wmt7fO&md5=038fbc0fdf911ff02bcbac30822b8ca6CAS | 24123423PubMed |

[27]  D. Yadagiri, P. Anbarasan, Org. Lett. 2014, 16, 2510.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmtVegsbk%3D&md5=cb5e1e139a13ee8d3b661d97bcfa5553CAS | 24724575PubMed |

[28]  T. Miura, Y. Funakoshi, M. Murakami, J. Am. Chem. Soc. 2014, 136, 2272.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXpslGgtQ%3D%3D&md5=d19882c995acd496deafa1cad586f06aCAS | 24437578PubMed |

[29]  J. S. Alford, J. E. Spangler, H. M. Davies, J. Am. Chem. Soc. 2013, 135, 11712.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFOlsbfE&md5=c0b706b30aa84deaa384048ab1e3663eCAS | 23915171PubMed |

[30]  T. Miura, T. Tanaka, K. Hiraga, S. G. Stewart, M. Murakami, J. Am. Chem. Soc. 2013, 135, 13652.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtlGntbnM&md5=fac1739fb85b6d439260c2f8c7c35f97CAS | 23988194PubMed |

[31]  B. Rajagopal, C. H. Chou, C. C. Chung, P. C. Lin, Org. Lett. 2014, 16, 3752.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVKnsLrE&md5=f3d358d915cfdcd8717b7e5660419d75CAS | 24968224PubMed |

[32]  E. E. Schultz, R. Sarpong, J. Am. Chem. Soc. 2013, 135, 4696.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjslGhsbk%3D&md5=398fc522f1d985d478094ede71adefa0CAS | 23477843PubMed |

[33]  H. D. Xu, Z. H. Jia, K. Xu, H. Zhou, M. H. Shen, Org. Lett. 2015, 17, 66.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitV2nt7%2FE&md5=a836bacb068bedc30280db65fe1ac114CAS | 25496025PubMed |

[34]  W.-B. Zhang, S.-D. Xiu, C.-Y. Li, Org. Chem. Front. 2015, 2, 47.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitVWhtrfO&md5=13fd83126b701e3e7fcf41951207edc0CAS |

[35]  A. Boyer, J. Org. Chem. 2015, 80, 4771.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmslOitb4%3D&md5=9bd98c4f26ce7d27e54d8d89daa0654cCAS | 25891197PubMed |

[36]  N. Selander, B. T. Worrell, V. V. Fokin, Angew. Chem. Int. Ed. 2012, 51, 13054.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslSrsLvE&md5=1b27e95c453fcd3449249794c7770e99CAS |

[37]  N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xht1CisrfF&md5=8fa4cbcd545dd8551fddb2f4862423fcCAS | 22913576PubMed |

[38]  Y. Xing, G. Sheng, J. Wang, P. Lu, Y. Wang, Org. Lett. 2014, 16, 1244.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisVWhs78%3D&md5=c73b33d478c34f403d3089ecda628418CAS | 24517549PubMed |

[39]  H. M. Davies, J. S. Alford, Chem. Soc. Rev. 2014, 43, 5151.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtFWhsL3F&md5=4640833be321b1a0facdb82afa8adce4CAS | 24802192PubMed |

[40]  P. Anbarasan, D. Yadagiri, S. Rajasekar, Synthesis 2014, 3004.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvFSlsr%2FF&md5=b1f5f3766f2be3da2383f0f5ff0f7836CAS |